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http://dx.doi.org/10.5012/bkcs.2013.34.6.1741

Efficient and Regioselective Ring-Opening of Epoxides with Alcohols and Sodium Azide by using Catalytic Amounts of GaCl3/Polyvinylpyrrolidone  

Pourali, Ali Reza (School of Chemistry, Damghan University)
Ghayeni, Samaneh (School of Chemistry, Damghan University)
Afghahi, Fatemeh (School of Chemistry, Damghan University)
Publication Information
Abstract
A new polymeric catalyst was prepared by supporting $GaCl_3$ on cross-linked polyvinylpyrrolidone ($GaCl_3$/PVP). This catalyst was employed for efficient and regioselective ring-opening reaction of epoxides by various alcohols under solvent-free conditions at room temperature. In our procedure, this heterogeneous catalyst was used at neutral and mild reaction conditions to afford high yields of ${\beta}$-alkoxy alcohols. Also, regioselective conversion of epoxides to ${\beta}$-azidohydrines was accomplished by sodium azide in MeOH in the presence of $GaCl_3$/PVP at room temperature. $GaCl_3$/PVP is a non-hygroscopic and recoverable catalyst and is easily separated from reaction mixture by a simple filtration and re-used repeatedly. Also, this catalyst has good handling and can be stored for long time without any reducing of its reactivity.
Keywords
Alcohol; Epoxide; Gallium trichloride; Ring-opening; Sodium azide;
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Times Cited By KSCI : 3  (Citation Analysis)
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1 Zakavi, S.; Abasi, A.; Pourali, A. R.; Rayati, S. Bull. Korean Chem.Soc. 2008, 29, 866-868.   DOI   ScienceOn
2 Pourali, A. R.; Ghanei, M. Bull. Korean Chem. Soc. 2006, 27,1674-1676.   DOI   ScienceOn
3 Pourali, A. R.; Ghanei, M. Chin. J. Chem. 2006, 24, 1077-1079.   DOI   ScienceOn
4 Pourali, A. R.; Tabaean, M.; Nazifi, S. M. R. Chin. Chem. Lett. 2012, 23, 21-24.   DOI   ScienceOn
5 Pourali, A. R. Mendeleev Commun. 2010, 20, 113-115.   DOI   ScienceOn
6 Iranpoor, N.; Firouzabadi, H.; Pourali, A. R. Synthesis 2003, 1591-1597.
7 Yamamato, H. Lewis Acids in Organic Synthesis; Wiley-VCH: New York, vol. 1, 2000.
8 Kobayashi, S.; Manabe, K. Pure Appl. Chem. 2000, 72, 1373-1380.   DOI   ScienceOn
9 McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275-3300.   DOI   ScienceOn
10 Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217-3274.   DOI   ScienceOn
11 Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 103, 3401-3430.   DOI   ScienceOn
12 Galaffu, N.; Sechi, G.; Bradley, M. Mol. Div. 2005, 9, 263-275.   DOI
13 Bhattacharyya, S. Mol. Div. 2005, 9, 253-257.   DOI
14 Jamieson, C.; Congreve, M. S.; Emiabata-Smith, D. F.; Ley, S. V. Synlett 2000, 1603-1607.
15 Nagendrappa, G. Resonance 2002, 59-68.
16 Kobayashi, S.; Busujima, T.; Nagayama, S. A. Chem. Eur. J. 2000, 6, 3491-3494.   DOI   ScienceOn
17 Crich, D.; Fuchs, P. L.; Molander, G.; Charette, A. B. e-EROS Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: 2010.
18 Yadav, J. S.; Reddy, B. V. S.; Biswas, S. K.; Sengupta, S. Tetrahedron Lett. 2009, 50, 5798-5801.   DOI   ScienceOn
19 Yadav, J. S.; Reddy, B. V. S.; Bhasker, E. V.; Raghavendra, S.; Narsaiah, A. V. Tetrahedron Lett. 2007, 48, 677-680.   DOI   ScienceOn
20 Tobisu, M.; Ito, S.; Kitajima, A.; Chatani, N. Org. Lett. 2008, 10,5223-5225.   DOI   ScienceOn
21 Zakavi, S.; Abasi, A.; Pourali, A. R.; Talebzadeh, S. Bull. Korean Chem. Soc. 2012, 33, 35-38.   DOI   ScienceOn